The Five Times Felicity Worked Late And The One Time She Didn't
by Megget18
Summary: Felicity Smoak has no problem working overtime especially if it means spending a little extra time with boss, friend, (and sometimes crush?) Oliver Queen. There's something about working late that seems to bring them closer together, so what has enough pull to keep her away from that even once? Six one-shots focus on the friendship and feelings between our favorite hero & IT girl.
1. Adventures in Squatting

**The Five Times Felicity Worked Late and the One Time She Didn't.**

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_Author's Note: Hey guys, this is going to be a new series of Arrow one-shots that I plan on writing. As the title indicates there will be six in total. For a few of them, I'm doing my take on common tropes we find these two in (like Oliver training Felicity) and what not. I hope you enjoy them. Just FYI, there may be some time between chapters since I have other stories that need my focus too, but I hope you enjoy them!_

**_Disclaimer: I do not own any part of Arrow._**

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Adventures in Squatting

Oliver pulled the heavy door closed behind him and took a relieved breath. The door effectively shut out the noises of the crowded club and allowed him to escape the night that was still in full swing. He breathed in through his nose, relishing in the silence only to realize that it wasn't as silent as he thought it should be. He moved quietly, easily sliding into superhero stealth mode as he moved to investigate the source of the noise.

Oliver reached the bottom of the stairs and absorbed every part of the room as he was trained to do. His eyes traveled back past the surveillance and exercise equipment to a dark corner of the room where they landed on the distant blonde head peaking out over an old couch that he never even realized was down there.

He approached slowly, aware that she hadn't moved once since he spotted her—aware that he could be walking into some kind of trap. His eyes flitted to all edges of the room, assessing all possible threats. He was so hyperaware of everything else that he didn't notice when the blonde realized that he was there.

"What are you doing?" Felicity asked as she looked quizzically in the same direction that he had been staring.

Oliver snapped his head towards her – it was the only indication that she had startled him. He immediately straightened up and cleared his throat, realizing that he had over-reacted.

"Me? What are _you_ doing?" He looked around the room as though expecting Diggle to pop up from the shadows. "For once, you don't need to be here. We were supposed to be taking a night off from Arrow duty."

"So you decided to practice creeping around the Foundry?" She raised her eyebrows above the rim of her glasses.

Felicity set down her tablet and leaned forward to tap the spacebar on one of the several laptops that she had spread out between the couch and the floor, effectively pausing the episode of Game of Thrones that she had been watching. It seemed Oliver had found the source of the noise.

"I heard something," Oliver explained simply in the efficient manner he was accustomed to.

She gave him a half smile. "Just me."

He let the words hang in the air, not quite sure where to go from there. His brain was fried from a long day and he hadn't been prepared to interact with anyone for the rest of the night.

Felicity couldn't stand the silence. "If you came down to work out, you won't bother me. Feel free." She looked up at him, craning her head to keep eye contact. It was a very uncomfortable position.

Oliver looked over at the salmon ladder and sighed. "Uh, no that's not why I came down."

Felicity shifted so that she was sitting straight up. She rearranged her computers, making space on the couch. "Did something come up? Do you need me to track something down?" She adjusted her glasses, ready to focus on saving the city.

"No. No, Felicity, it's nothing. I didn't know you were down here." Oliver braced his hands against the back of the couch and looked closely at the various computers scattered everywhere.

"Is that a hint for me to leave? Because I really don't want to. In fact, I will probably just ignore you."

Oliver failed to hold in a smile. "What are you doing down here anyway?"

"Catching up on some Queen Consolidated work – it builds up when I spend my night watching your ass." She cleared her throat. "Back! I meant watching your back…" She shook her head, trying to bypass her Freudian slip. "I promised a few people I would lend them my IT expertise."

"Aren't you burnt out?" he asked, voicing the very feeling that was plaguing him.

"No, it's kind of nice getting back to the grind. This stuff is easy compared to what you give me."

"And that?" he asked, pointing to the paused DVD player.

"Also catching up on Game of Thrones."

Oliver narrowed his eyes. He had no idea what she was talking about.

She made an incredulous gasping sound and twisted all the way around so that she could face him, "Oliver, enough is enough! You've been off the island for way over a year now. Catch up with pop culture already!"

"If you haven't noticed, I'm a little busy."

"Ya know life is going to get pretty lonely if you keep living on the outskirts of it."

Oliver knew that she hadn't meant to hit any hard spots, but something about it struck a cord. It's why he had found his way to the Foundry tonight. He wanted a break from the world that he didn't feel he fully fit anymore—the world he couldn't simply live in. So he went to a place outside that world to feel comfortable. He found himself on an island again, except this one was one he made.

He glanced down at Felicity. At least he wasn't alone.

Felicity grabbed his arm, trying to shake him out of his thoughts. She pulled him around the arm of the couch (obviously he let her do so) and guided him to sit beside her. "I can give you a crash course. I've read the books too so absolutely any questions you have I can answer." She told him as she rose and found one of the extra tables stored down there for Verdant. She pulled it over in front of the couch so that she had some place for the laptop to sit.

"Answer this: why are you doing this _here_? While wearing _that_?" He asked as she moved around. He had just really noticed that she was dressed from head to toe in what looked to be a really comfortable set of flannel pajamas.

She looked down at herself like she too had also just noticed what she was wearing. "Right, well the apartment above mine flooded their bathroom and caused a big soft spot in my ceiling. It takes a few days to fix so I thought I could camp out here."

Oliver just gave her a blank stare. He blinked several times trying to figure out exactly how he should respond first. He went with anger.

"Felicity, are you insane? Of all the places you have to crash, you chose the Glades. It's not safe here."

She quirked her head to look at him and stood up straight from pulling the table into position. "It's not safe in your secret underground superhero layer?"

Oliver balked. "I don't like the idea of you being here at night without me. Of you hanging around the Glades more than you have to."

"Well you don't have to worry then because you're here." She smirked and flopped down next to him.

Oliver gave a long sigh and the frown lines around his mouth decreased. "Please don't stay here."

Felicity crossed her arms over her chest. She didn't want to give in, but she felt bad that she was worrying him. "Come on. I like it here. All of my girlfriends have multiple roommates and I knew it would be nice and quiet here. Dig and Lyla are still getting…reacquainted. This place is perfect. I can work and play." Oliver raised an eyebrow at her. She leaned forward and picked up the laptop with the paused television show. "You can play with me," she said in a sing-song voice until she realized what she had said. She coughed a few times as if to clear the awkwardness from her voice.

Oliver took the computer from her and set it aside. "Why wouldn't you ask me?"

"Ask you what?"

"For a place to stay. There's always room for you at the mansion." He touched her arm softly in that sincere way that always made her listen.

"Of course. I knew you'd offer, but you already have a lot going on in your life. You don't need me all in your business."

"I don't mind you being in my business. I usually prefer it—it tends to keep me alive."

She gave him a wide grin. "I just figured it would invite more questions than we needed – with Thea and your mother. And I already get enough looks at work from my sudden rise in the company."

Oliver narrowed his eyes. "Do people say things to you?" he asked it calmly, but she could tell by his clenched fist that he was anything but.

She tapped at his fist to get him to loosen up. "Put the arrow back in the quiver, hot-head. It's nothing that I can't handle."

"You know you can come to me if you need help with any of it." He said, ducking down to make sure that he caught her eye.

She nodded. "I know and I appreciate it." She tucked her legs under her body. "Now, tell me why you came down here when there is a whole club full of people who would love to party with you upstairs."

"Mainly to escape the whole club full of people who would love to party with Oliver Queen."

Felicity rested her head against the couch cushion as she took him in. "I guess I can see how that could be annoying."

He tried to shrug it off. "It's just part of the job."

"Is that how you see your real life? As a job?"

Oliver shook his head. "That isn't my real life—it's my public life. And yea, it's my job."

That bothered Felicity. "Then what is real for you? And I mean your life away from all the work. Because as good and necessary as it is, being the Arrow is a job too."

Oliver never really considered that. "It may be a job, but it's where I feel comfortable—like myself. It's real. My family life—that's real. And ya know, down here. Dig and…and you—you guys help me in more ways than you know."

"I wish you didn't have to hide who you are," she said almost wistfully. She hadn't meant to voice that thought aloud.

"It's worth it." There was a long moment where nothing was said, just silent agreement. Then Oliver cleared his throat. "Alright, time to fill me in on your pop culture stuff—tell me about this show, Professor."

"Oh, I am on top of you—erm, it!" Felicity exclaimed as she pulled the laptop to her. She lit up as she went over every detail between the show and the book that she could remember. She was only halfway through the first season herself, but she had up to the current season on DVD. Oliver watched her talk in quiet amusement. She finally got to the exact place where she had paused the show and was ready to start it up again. She stopped herself.

"What's wrong?"

"I am suddenly remembering the number of graphic sex scenes in the show thus far," she admitted.

Oliver laughed. "I think I can handle it."

"I'm not sure I can."

He laughed again and pushed the play button for her.

Felicity settled back into the couch stiffly while waiting for the next sex scene to appear. It didn't take long. She held her breath and tried desperately not to look at Oliver even though it killed her not to see his reaction. Her heart was beating wildly and she started to sweat. She didn't know why she felt so embarrassed, but it was like she was back in high school.

When it was over, she finally breathed again. She kept her eyes glued to the screen though.

"You okay?" he asked.

"Mmmm Hmmm."

She could feel him smiling. She did not approve of his enjoyment of her discomfort. She yanked a pillow out from behind her back and smacked him with it.

"Hey!" he guffawed.

"Oh, shut up!"

"Is this any way to treat your boss?"

"I think you can handle it."

Oliver settled the pillow behind his head and turned his attention back to the show. The rest of the night was spent much the same. They watched episode after episode well into the night, stopping only to talk briefly about this and that. They lasted well after the final club goer had gone home until the credits on the sixth episode that they watched together rolled with neither one of them awake to play the next one.


	2. Training Time

**The Five Times Felicity Worked Late and the One Time She Didn't.**

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_Author's Note: Hey guys, been awhile. Here is the next part in this series. Just so you know I'm not necessarily following the current arc of the show-these are just specific scenes or tropes I've wanted to take a crack at so they may conflict with what's currently going in the actual show. I hope you enjoy! Also, for those who read Heroes & Sidekicks, I'm working on the next chapter now and it will be out very soon!_

**_Disclaimer: I do not own any part of Arrow._**

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Training Time

"I think I changed my mind," Felicity said as she backed slowly away from an approaching Oliver.

Oliver stopped walking and held his hands up in the universal sign that he was backing off. "I'm only doing this because you ordered me to."

She set her hands on her waist. "Asked, not order."

"I care to disagree," Dig chimed in from his perch on Felicity's desk.

"I didn't ask you, Dig." She scowled.

"No, you asked _him_. So stop being a wimp," Diggle said. He slid off his desk and went to retrieve his jacket. "You'll be fine, Felicity."

"Are you leaving?" she practically squeaked with panic.

"Hell yea, I am. It's late and if I'm lucky I can get home in time for a late dinner with Lila. You two don't need me right now."

Felicity brushed past Oliver to stand face to face with Diggle. "John, I would really prefer it if you stayed," she pleaded.

"You should have thought of that before you asked him to train you instead of me," Diggle teased. He placed one hand on each of her shoulders. "Stop worrying. And try to get a few hits in." He squeezed her lightly and headed for the Foundry's stairs.

Oliver walked up behind Felicity quietly as she watched Diggle leave. "You don't actually think that I'm going to hurt you, do you?" he asked so close to her ear that she could feel his breath on her skin.

She jumped at his voice and spun around, pressing a hand to her spiked heartbeat. "Not on purpose."

"I have very precise control of my body."

She let her eyes travel up and down his torso. "So I've seen." She cleared her throat and directed her gaze back to his face.

"I would never let you get hurt," he promised.

"I know."

"Then what is going on with you?"

Felicity sighed. It had been a week since she had asked Oliver to train her personally. It was after yet another stint as a hostage and Oliver swinging in to save her once again. She appreciated the effort, but she was sick of the situation.

Clearly her training with Diggle wasn't working fast enough. Dig was a great teacher—very patient, but she knew that sometimes he let her off easy. Oliver wouldn't do that. She needed someone who could challenge her in every way—maybe even teach her how to fight dirty with his jungle warfare moves. The precise military moves from Dig weren't getting her very far.

When she first suggested the idea to Oliver weeks before, he had refused. It only took three times for her to bring it up before she threw out a line that he couldn't ignore.

"I just figured I should learn more of a street style of fighting. You never know when another one of your girlfriends is going to turn on you. Isabel is already shifty – I think you would be best suited to prepare me." She could admit to herself that the comment was unnecessarily sassy and probably undeserved. But it got Oliver's attention.

He agreed to train her then, probably more out of spite than anything else.

And at first she was really satisfied with herself for convincing him…until she realized what it would entail. It wasn't the fighting so to speak that she was freaking out about – she truly wanted to learn.

It was the fact that she and Oliver would be physically closer than she ever thought would truly happen. Both would be wearing minimal clothing with a lot of sweating and grunting going on. That was a bit overwhelming.

She never had a problem in that capacity with Diggle. Sure, he was ridiculously handsome and muscley, but she had always seen Dig as more of a big brother. It helped that during the first time that she had _really_ talked or spent anytime with the man (as someone other than Oliver's shadow or the Hood's "doctor"), it had become clear to her that he was in love with Carly. That didn't give her much of a chance to crush on Dig—even if the couple didn't last—before she started seeing him as a brother. She didn't have that problem with Oliver. By the time she knew about all of Oliver's various women (Laurel especially), she was well on her way to becoming one herself. The first time they met she was thrown off by how attractive he was. The boldface lies he had fed to her helped stop her babbling and kept her suspicious. With every meeting, his lies got worse. It would have been endearing if it weren't so incredibly annoying. Still he was always nice to look at.

Now was no exception to that. All he had on was a pair of sweatpants that hung low off his hips. She could see every scar on his chest and the tattoo that covered his heart. She had yet to learn what it meant. He was focused completely on her, blues eyes trained on her like she was a target trapped in his sights. And they were totally alone.

"I didn't think this through."

Oliver crossed his arms. "Think what through?"

For once she shut her mouth, desperate to keep in the thoughts about his naked torso that threatened to spill out of her lips. "Nothing. Fine, let's do this."

Felicity took a few quick breaths and shed the sweatshirt that she was wearing over her workout clothes. She pulled her hair back into a ponytail. She had already exchanged her glasses for contacts—she shivered again remembering the feeling of touching her eyeball. She hated it.

When she looked up at Oliver again, she found him smirking at her.

"What?"

"It's kind of cute seeing you so out of your element."

"I'm taking that as an insult." She huffed.

"Take it any way you want." He laughed and ushered her forward. She complied.

He spent the first fifteen minutes or so just teaching her slow warm-up stretches—ones that wouldn't be helpful in the field, but that she could do everyday to keep her body ready. It involved minimal touching, which helped ease her nerves.

Then he switched gears.

"To be honest, I've never really trained anyone from the ground up before so I'm not sure what the best approach is," he admitted.

She interrupted his train of thought. "Well, how did your training start?"

Oliver paused. Actually, he froze—like his entire body had just powered down. An image of Shado flashed through his head and he had to push it back to that endless cavern of his mind that contained all of his memories from the island. "Why?" he snapped.

Her teeth clacked together in surprise at his tone, but this time she couldn't keep her mouth closed. She realized that she had never asked him directly about the island before. She had actually been pretty proud of herself for holding back for so long. It was an accident tonight. It had just slipped out and she hadn't even realized it until he reacted so weirdly. "Because that's one of the reasons that I asked you. Dig is a military man – he's used to training athletic and disciplined people. From what I've heard of your glory days, that wasn't exactly you and it's definitely not me." She shrugged. "I figure if you can teach me a microcosm of the training you had, I'll be able to protect myself just fine."

Felicity saw the way he physically loosed the tension he had bunched in his shoulders. She thought it was funny that such a throwaway question to her held such meaning to him. She hadn't meant to delve into his island life. She just wanted to know the logistics of how he had trained physically.

Oliver cleared his throat. "I slapped water."

Felicity raised her eyebrows, which scrunched her forehead in what Oliver thought was an admittedly cute expression of confusion. "Excuse me? Is that a euphemism for something?"

Oliver laughed, remembering how ridiculous he had thought the exercise was when Shado first made him do it. "No. I sat on a grimy floor for weeks and slapped water."

"Well, I was right. That sounds easier than what Diggle put me through. I'm not really sure I see the endgame though."

"I did it long enough every day until I was strong enough to pull back on my bow. And I didn't even realize what she was doing until it was done."

Felicity had the biggest urge to ask about the 'she' that he was referring to, but she knew that it was the wrong move. She knew that there had been other people with him on the island. She also knew that he hated talking about them. He would have to be the first one to broach the subject.

"I guess that's good with the stretches you showed me—they'll make me stronger if I do them every day. But water-wise, I wasn't really planning on wielding a bow any time soon."

"Yes, if I recall correctly you think archery looks utterly ridiculous." Oliver remembered as he took a step closer to her.

She bit her lip. She remembered saying that before she knew about his nighttime hobbies—it seemed like a million years ago. "To be fair, I said that before I knew you were into that stuff."

"And you still think that?" he asked as he circled around her, trying to figure out how to approach the next part of the training.

"No, you make it look good," Felicity blurted out as she tried to keep her eyes on him when he slipped behind her. "What I meant was…" She cleared her throat, but it didn't help her think, "something else." She cringed at her lack of forethought.

"We should get back to training."

"Yes, thank you."

"Alright, I know Dig had already gone over some basic forms and moves with you. We're going to go with a more self-defense based approach."

Felicity nodded and felt him hovering behind her.

"So I'm going to grab you and I want you to instinctively react. Once I know, I can correct you and show you some ways to disengage."

Felicity barely had time to process what he said before his arms were wound tightly around her. She immediately tensed up. This was exactly what she had been worried about. His arms felt particularly snug and warm.

"Well?"

"Well what?"

"You're supposed to react instinctively."

"You're hugging me—this _is_ my natural reaction."

She could feel his ab muscles contract as he sighed. "I'm not hugging you, I'm attacking you."

"I've seen you attack people. This is not how you do it."

"Would you like me to actually attack you?"

Felicity paused for a long moment. "No."

"Then try to throw me off of you."

Felicity gritted her teeth as she heaved her weight to try and flip Oliver off of her. He barely moved. Her next attempt was to simply pry his hands off of her, but it was like they were soldered on. Her breathing was becoming labored and it was only partially due to physical exertion. She tried to elbow him in the stomach and actually got a grunt out of him before he hugged her tighter so that her arms couldn't move. Her only other option was to try and stomp on his feet. She slammed her foot down, but he dodged her. She tried again, but failed. And every time she did it, she felt more and more uncomfortable. She was basically wiggling against part of Oliver that she couldn't thinking about at the moment without physically combusting.

"I got nothing," she finally said.

Oliver loosed his grip slightly. "This is a little sad."

Felicity slammed her elbows back in frustration. She surprised him so much that he almost dropped his hands from her. It was enough for her to slip under than and duck away. "Better? She asked, voiced soaked with snark.

He glared at her. "I thought you gave up."

"Strategy." She shrugged.

"You're gonna need more than that," he said as he beckoned her toward him with one finger.

He spent most of the next hour teaching her precise movements to break a hold from behind—the most likely position a hostage-taker would yield. He would go over them slowly and then speed up more and more until she had the move down. She was so focused on what her was teaching that she almost forgot about his constant contact. Almost.

"Alright, this one's a little more complicated," he told her. "You're going to tuck your chin in between the arm I have across your chest. Then you are going to try to step on my insole as hard as you can while at the same time yanking my arm down from your chest. Do it right and you will be able to duck left under my arm and spin to face me. Then as quickly as possible pull my arm forward—the one that was on your chest that you should still have a good grip on." Felicity nodded as she memorized each step individually and tried to map out the picture in her head as a whole. "The goal is to get me off balance. Get me off balance and you have a chance of getting away."

Felicity nodded and flexed her muscles as she got ready to try this out. It was safe to say that she was not exactly confident that she could pull this off.

Oliver wound his arms around her, his grip as strong as ever. She paused, taking a few quick breaths to psych herself up.

At just about the point that she had gotten a little too far in her own head, she felt him shift. He leaned down so that his mouth was just outside her ear. "You got this," he whispered.

She sighed deeply and before she had another second to over-think it, she drove her heel into Oliver's insole and yanked his arm from her chest. It had gone so well up until that point, but it fell apart all too quickly.

Looking back she thought that she may have spun too early—she thought that maybe she was supposed to have stepped forward first and then spun to face the attacker. Whoops. Instead she just spun on him, causing limbs to tangle with limbs and her forehead to smack into his chest. She spasmed a bit as she tried to pull free and clear from his body, but she misjudged her own aptitude for balance. She flung herself backward, but one of her feet was still trapped among his legs and no extent of flailing arms could keep her from falling backwards.

Oliver saw everything that was happening and his lightening reflexes took over. It would always be in his instincts to 'save' Felicity. No matter what. He reached for her arms to pull her to her feet, but her own efforts to save herself thwarted him. She knocked his arms away and distracted him enough to kick his legs out from under him. He fell forward—it was either that or step on her to catch his balance—and followed her to the ground. He fell on top of her, throwing his arms out just in time to catch himself from thudding against her. He hovered over her as they both caught their breaths.

Felicity stared up at him as he searched her face for any signs that she was okay. She smiled at him sheepishly. "I'd say that I definitely got you off balance."

"This isn't exactly a better position to be in," Oliver countered.

"Looks good from down here," she said under her breath.

Unfortunately Oliver was only inches from her face and clearly heard every word. He didn't ignore her awkward comment as he usually did. Instead he laughed and she could have sworn that he let his eyes momentarily fixate on her lips. It seemed as if laying on top of her was giving him some ideas. She didn't exactly mind it.

His eyes traveled back up to her own—it was weird to adjust to seeing her without the glasses. He wasn't sure which look he liked batter—hell, she looked good either way. "Are you okay?"

Her gaze flitted down to his bare chest. "I've been worse."

When their eyes caught again, there was a moment when Oliver wasn't quite sure what was going to happen. He had lost his hold over the coil of feelings that he kept wound so tightly. It was terrifying and thrilling and completely unexpected. He wanted to do it in that moment—to take the plunge and kiss her. If only to know what it would be like.

He was pretty sure she'd be game.

But he didn't. He couldn't risk it. There was too much to lose—their friendship, their partnership, their team. He couldn't risk her heart…or his.

Would one little kiss be worth it?

Oliver swiftly pushed away from Felicity and to his feet. He held out his hand to pull her up after him and she complied.

"I think that's enough for tonight. We can work on that more another time."

Felicity nodded and went to get a drink. "Fair enough," she answered. She knew something had happened with Oliver—saw a strange moment in his expression when he was hovering over her. He had looked at her in a way that she had never seen him look at her before. It gave her chills. She wasn't sure if it was a good thing or a bad thing. She already had enough trouble concentrating around him. Now all she could do was remember that look.

"We can do another session tomorrow afternoon," Oliver informed her. He tossed her a towel.

She nodded. "Maybe we can start with some weapons tomorrow. I think that would be safer."

"Weapons are safer?" Oliver directed the question to her back as she retreated to get changed into normal clothes. He was genuinely confused.

"Yes, less potential for touching," she answered in a voice quiet enough that she didn't think he would hear her.

But as always he did and he had to agree that touching Felicity was definitely more of a danger to him than any weapon he could find in the Foundry.


End file.
